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Order of operations in Tax loss harvesting - buy then sell vs. sell than buy

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  • Order of operations in Tax loss harvesting - buy then sell vs. sell than buy

    Assume that I tax-loss harvest according to IRS rules:
    Sell a stock and don't repurchase it for >30 days in all my accounts
    Don't buy a substantially identical stock to the one just sold i.e., I choose something that tracks a different index like VTI for VOO
    Have automatic dividends off so I don't accidentally buy small lots at then end of the year.


    I have cash available due to my IPS for my emergency fund and estimated taxes.


    Scenario 1:
    Sell VTI at a loss, then purchase VOO - to keep assets allocation similar.


    Scenario 2:
    Buy VTI at current low price from cash in bank, then sell via Spec ID a lot of VTI at a loss [leave in cash to fund emergency fund/quarterly taxes]

    I understand the 30 day wash sale to be triggered by the sell trade. So why do people sell then buy instead of buy then sell? Cash flow?

  • #2
    If I am understanding your question, you don't realize the 30 day window applies to both before and after the sale.
    Scenario 2 would be a wash sale

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    • #3
      I was wrong. I didnt understand 30 days prior to trade too.

      I find it hard to do a tax loss harvest as I buy vti at least once a month per my IPS

      Comment


      • #4
        Originally posted by runfast00 View Post
        I was wrong. I didnt understand 30 days prior to trade too.

        I find it hard to do a tax loss harvest as I buy vti at least once a month per my IPS
        https://www.whitecoatinvestor.com/tax-loss-harvesting/

        Example: If you bought VTI two weeks ago and it drops a lot you can sell all of the VTI you bought two weeks ago + older shares of VTI. As long as sell all the shares you bought prior to the 30 days you won't trigger a wash sale.

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        • #5
          Originally posted by runfast00 View Post
          I was wrong. I didnt understand 30 days prior to trade too.

          I find it hard to do a tax loss harvest as I buy vti at least once a month per my IPS
          In that case you could instead continue to buy voo (or similar) while in 30 day window. Or save cash until out of window

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          • #6
            Just sell all the shares you bought in the last 30 days. Make sure you aren’t reinvesting dividends into the funds as that gets a lot of people, too.

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            • #7
              Originally posted by zlandar View Post

              Example: If you bought VTI two weeks ago and it drops a lot you can sell all of the VTI you bought two weeks ago + older shares of VTI. As long as sell all the shares you bought prior to the 30 days you won't trigger a wash sale.
              Probably semantics, but just to clarify, I think zlandar is meaning to say:

              ”As long as you as sell all the shares you bought during the prior 30 days you won't trigger a wash sale.”

              You can then also selectively choose any losing lots you purchased prior to the 30 days.

              Btw, I did my very first TLH today, selling some VXUS and buying some VEU.

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